We Tasted And Ranked Pepperidge Farm's Entire Holiday Cookie Collection

As the holidays usher in their unmistakable spirit of joy and celebration, our senses are beckoned by the delectable allure of seasonal treats. In this culinary exploration, we turn our attention to one of the most renowned purveyors of gourmet cookies -– Pepperidge Farm. With a legacy steeped in craftsmanship and a commitment to quality, Pepperidge Farm's holiday cookie collection stands as a testament to the artistry of indulgence.

I took on the task of ranking the company's holiday cookie selection so you can have an array of options to choose from for your upcoming celebrations. From Milanos to Pirouettes and everything in between, I dove into every cookie variant to uncover the nuances of each, offering a discerning perspective on what makes the ultimate Pepperidge Farm holiday cookie. Taste, shapes, textures, and holiday themes were all taken into account, offering you the analysis you need for your cookie-buying quests. May the best cookie win.

Some recommendations are based on first-hand impressions of promotional materials and products provided by the manufacturer/distributor/etc.

A brand new take on Pepperidge Farm's Chessmen is here with its new limited edition Holiday Nog cookie. The minute you open the bag, you're greeted with the smell of spice and butter — a welcoming aroma.

True to its shortbread roots, the Holiday Nog cookies encapsulate the sugary essence of eggnog, boasting a robust and buttery foundation. However, as we navigate the hierarchy of Pepperidge Farm's holiday cookie lineup, the Holiday Nog finds itself at the bottom of the list. While undeniably rich and embodying the seasonal flavors we associate with eggnog, these cookies venture into the territory of overwhelming sweetness.

For me, the Holiday Nog cookies verge on the cloying side, with a coating of sugary eggnog flavoring that, unfortunately, misses the mark. The advice here is straightforward: when it comes to eggnog, perhaps it's best enjoyed in liquid form. In the ever-evolving landscape of holiday treats, the Holiday Nog cookies serve as a reminder that not every venture into uncharted flavor territories is an unequivocal success.

As a devoted Milano enthusiast, venturing into the uncharted territory of Milano Slices held both excitement and anticipation. Alas, the experience proved to be a touch underwhelming, and it's with a discerning palate that we place the Peppermint Milano Slices at spot number 13 in our ranking.

Fans of Milano cookies may be familiar with the minty iteration and find themselves puzzled by the Peppermint Slices. The expected burst of refreshing mint was notably absent, leaving a void in what should have been a harmonious blend of chocolate and peppermint. Instead, the dominant flavor profile leaned heavily on the chocolate, offering a taste that, while pleasant, deviated from the anticipated peppermint-infused delight.

One of the hallmark features of the classic Milano — the sumptuously buttery wafer — also seemed to lose its impact in the transition to the sliced format. The wafer, though present, lacked the thickness and soft texture that typically follows the initial bite. This departure from the expected texture was a noticeable departure from the cherished Milano experience.

In essence, the Peppermint Milano Slices emerge as a concept that excites on paper but falters in execution. The absence of a robust peppermint essence and the deviation from the signature Milano texture create a dichotomy between expectation and reality. It's as if these slices tantalize with the promise of a festive treat but ultimately fall short of delivering the anticipated holiday magic.

As a dedicated fan of pirouettes, Pepperidge Farm really nails it. The delicate, flaky layers of the cookie shell mixed with an array of smooth and creamy fillings is spot on. I have to say, the brand's version of the Chocolate Hazelnut Pirouette is undeniably commendable. 

Yet, the pivotal turn in this pirouette tale is a matter of personal taste, especially when compared to the illustrious array of other pirouette flavors crafted by this popular brand. The infusion of chocolate and hazelnut, while a classic pairing, just isn't my thing. The delicate balance that characterizes other pirouette variations seemed slightly askew in this rendition.

In the grand panorama of Pepperidge Farm's pirouette collection, the Chocolate Hazelnut variant emerges as a matter of preference rather than a critique of quality. It's a reminder that even within a beloved category of treats, taste is subjective, and individual inclinations play a pivotal role in the culinary experience.

Decorated sugar cookies scream Christmas in my eyes, so I was excited to give the Zurich Sugar Cookie holiday option a try. The visual allure of these cookies, dressed in vibrant red sugar, promised a sweetness that, unfortunately, didn't entirely materialize upon the first bite. While the sugar embellishments contribute a hint of sweetness, there's an elusive quality missing from the overall flavor profile. Despite their "sugary" base, the cookies fall short of the anticipated festive sweetness that defines a quintessential sugar cookie.

The lackluster nature of the cookie itself is a pivotal critique in this option. While not entirely forgettable, the Zurich Sugar Cookies lack the standout quality that sets them apart from the competition. They embody a sugary foundation that fails to evoke the jubilant response one might expect from a holiday sugar cookie.

Overall, I think the Zurichs would be great with a tea pairing, and if they were on a tray, I'd eat them. However, these definitely weren't a favorite. They just missed the mark in my sugar cookie book.

While fruity cookies aren't really my thing, there is something to be said about the Raspberry Linzer option. The inherent craftsmanship and thoughtful construction of these cookies are undeniable, transforming them into a well-executed treat within the holiday repertoire. 

The standout feature of the Linzer lies in its textural finesse. The cookies, soft and subtle, invite a delicate dance on the palate — a testament to the meticulous artistry synonymous with Pepperidge Farm. These treats boast a nuanced balance, offering a gentle respite from the bolder flavors that often characterize the holiday cookie lineup.

Digging deeper into this option, the raspberry filling tastes like a homemade jam, exuding a delightful tartness that plays in harmony with its decadent undertones. The result is a filling that transcends the standard expectations, elevating the Linzer cookie into a category of its own.

While these cookies may not have claimed the coveted title of a personal favorite, they command respect for their solid execution and sophisticated flavor profile. For those with a penchant for fruit, this one undoubtedly holds the potential to be a cherished delight amid the holiday festivities.

The Chocolate Fudge Pirouette gracefully breaks its way into the top 10, securing a commendable 9th place spot. As we unravel the layers of this confection, it becomes evident that this one is a study in delicate decadence, offering a nuanced combination of textures and flavors.

The exterior of this pirouette proves to be a testament to the art of cookie craftsmanship. Delicate and crunchy, it sets the stage for the sensory symphony that follows. A single bite, and the cookie yields with a softness that crumbles in your mouth, creating a harmonious textural experience.

One of the standout features of the Chocolate Fudge Pirouette is its impeccable cookie-to-filling ratio. The chocolate fudge filling seamlessly marries with the wafer, promptly taking over the taste buds without overpowering the delicate essence of the wafer itself. This careful balance ensures that both elements are allowed to shine independently while contributing to the overall indulgence of the snack.

Overall, the Chocolate Fudge Pirouette asserts itself as more than just good — it's a delightful encounter with a confection that knows how to strike the right chords. It may not be the best, but it certainly earns its place as a solid contender in the grand tapestry of Pepperidge Farm's holiday offerings.

For those with a penchant for buttery indulgence, the Chessman Butter Cookie is a top contender. As a self-professed enthusiast of butter cookies, the experience of the Chessman variant presented a mixed palate performance. 

The initial impression begins with a hard bite, deviating from the sometimes softer and more luscious textures characteristic of other buttery confections. The coating, an additional layer that wraps these cookies, introduces an intriguing element to the taste journey. While it contributes to the savory-sweet balance, it also veers away from the sometimes softer and more melt-in-your-mouth quality of traditional butter cookies. It's a characteristic that, while noteworthy, may sway those seeking a different textural experience.

The commendable aspect of the Chessman lies in its ability to strike a harmonious chord between savory and sweet flavor profiles. The butter and sugar create a nuanced balance that resonates with those appreciative of a well-crafted butter cookie.

My final conclusion is that these are good butter cookies, but there are better options out there when it comes to holiday treats. I'm not saying don't buy the Chessman, but keep reading for some real stand-out options.

The Double Dark Chocolate variant offers a generous serving of decadence, blending rich chocolate filling with the trademark Milano wafer in a symphony of flavor. The allure of this Milano option lies in its doubled indulgence — a feature that stands out prominently for enthusiasts of this classic treat. The amplified filling elevates the chocolate experience, allowing the distinct flavor to harmonize with the delicate wafer. It's a delightful play on proportions that caters to those who relish a robust chocolate profile.

While the Double Dark Chocolate undoubtedly earns its place as a solid cookie, it modestly steps into the shadows when compared to the flamboyant array of other holiday offerings. In a lineup bursting with festive flavors and intricate textures, these Milanos might be perceived as a touch more restrained, but a classic and dependable choice in a sea of seasonal experimentation, nonetheless.

As we navigate the delightful complexities of Pepperidge Farm's holiday treats, the Double Dark Chocolate Milanos serves as a reminder that sometimes, simplicity can be its own form of indulgence. If you grab these for a party, they will undoubtedly be a star. You can't go wrong with a classic chocolate Milano — ever.

The Amaretto Hot Cocoa Milano was a delightful surprise. Holding a flavor profile I normally wouldn't seek, these Milanos offered a well-balanced and gratifying cookie experience. You still get that classic buttery wafer and rich chocolate filling, creating a classic canvas. However, the amaretto flavoring, as promised, made an assertive entrance, offering a bold and distinctive note that might catch the uninitiated by surprise. The almond-infused essence, reminiscent of classic amaretto, presented a flavorful interlude that sets this Milano apart from its peers.

Yet, the true brilliance of this one lies in its ability to orchestrate a harmonious balance. As the initial boldness of the amaretto flavoring captivates the palate, a counterpoint emerges in the form of cocoa chocolate on the back end of the profile, mellowing out the almond-esque bite. This thoughtful interplay results in a well-rounded and sophisticated cookie experience, offering a unique and satisfying treat. Nice work here, Pepperidge Farm — definitely give these a try while supplies last!

If you like frosting, you're going to love the French Vanilla Pirouettes. These sugary treats emerge as an ode to nostalgia, evoking the delightful essence of birthday parties and celebratory cakes.

The crowning glory of these pirouettes lies in their generous application of filling, creating a luscious texture that envelops the wafer with a decadent embrace. However, this abundance of sweetness, while initially delightful, presents a caveat as the sugar builds up with each indulgent bite. As a word of caution, moderation is key, ensuring that the pirouette's enchanting sweetness remains a delightful treat rather than an overwhelming sugar rush.

These cookies have a special quality and stand as a testament to Pepperidge Farm's knack for encapsulating the essence of celebration within a slender wafer. While the sweetness may verge on the intense side after a few bites, the French Vanilla Pirouette is a delightful reminder that sometimes, the magic of a treat lies not just in its flavor but in the memories it invokes.

I love a good ginger snap and or ginger-flavored cookie, so I was ready and willing to try the Pepperidge Farm Gingerman. The initial encounter with these cookies revealed the classic attributes of a ginger snap — hard and crispy. When it comes to flavor, the careful balance of ginger and molasses is evident, offering a familiar flavor profile that is comforting in its predictability. It's the kind of ginger snap that promises a reliable, delicious experience without straying too far from the traditional path.

While undeniably good, the Gingerman does face a critique from those who seek a more pronounced kick of fire and spice from their ginger snaps. The gentle warmth of ginger and the deep richness of molasses, while present, may not reach the fiery heights desired by those with a penchant for a more intense flavor experience.

The Gingerman, in essence, embodies the sentiment of a well-executed classic. It doesn't attempt to reinvent the wheel but instead offers a dependable and enjoyable rendition of a beloved holiday treat. It may not have secured a top-three position, but it has certainly earned its place as a flavorful companion in the festive array of Pepperidge Farm's holiday cookies.

In this ultimate ranking of Pepperidge Farm's holiday confections, the Mint Chocolate Milano commands attention, securing a stellar 3rd place victory. For those who appreciate the art of a well-crafted mint cookie as the pièce de résistance after a sumptuous meal, these Milanos prove to be the epitome of post-dining indulgence.

Mint, often a potent force in the culinary world, is wielded with finesse in these cookies. The fresh flavor is just enough to elevate the profile without overpowering the ensemble. Paired with a harmonious union of a buttery wafer and a luscious chocolate coating, this trifecta of flavors coalesces in a symphony that is simply delicious. They are decadent enough that they kill your sweet tooth cravings but light enough that you can easily have more than one.

Pepperidge Farm showcases a mastery of restraint, allowing the essential components to shine in unison with the Mint Chocolate Milano. The result is an experience that is refreshingly straightforward, offering a minty embrace that enhances the post-feast ritual with an air of sophistication.

If we are talking surprise, Snowball Citrus is the winner. I normally don't love fruity cookies, so putting this one in second place was a real shock. But when Pepperidge Farm nails it, they really nail it.

The initial encounter with these cookies unveiled a delightful fusion of textures — a relatively hard exterior with a satisfyingly crunchy bite. As for flavor profile, the powdered sugar and subtle sugar cookie essence took the stage, setting the tone for the surprise that awaits — the notes of citrus.

The magic of this cookie lies in its ability to introduce the vibrant orange notes without overpowering the delicate foundational profile. This citrus infusion arrives as a harmonious interlude, gracefully weaving its way into the sweet cookie base. 

As the powdered sugar settles and the zesty afterglow lingers, it seems Pepperidge Farm might have indeed twisted my arm into discovering a new favorite. These are absolutely great and a must-try this holiday season. Seriously, don't take my word for it — give them a try.

Ranking number one are the Mint Brussels – a triumph of texture and taste that overshadows this entire list in my eyes. From the first bite, the Brussels reveal its winning card — the extraordinary texture that distinguishes it in the crowded landscape of seasonal options. The thin, uneven cookies on the top and bottom pave the way for a sensory experience that elevates the interplay of chocolate and mint to an art form. The best part — cookie doesn't overpower any other flavors and allows the delicate combination of mint and chocolate to shine. 

The Mint Brussels not only echo the familiar notes of its Milano counterpart but elevates the experience with an artful presentation and delicious filling. There was no doubt about it in my mind when I tried these cookies — these were the clear winner. From the chocolate and the mint to the unique cookie wafer, these are killer and will be in my house this holiday season.